Hi Reader,

Last week I asked what business decision or messy idea has been taking up more mental space than you'd like. A few of you replied, and one theme kept showing up: it's not that you don't know how to make the decision. It's that you get stuck before you even get there, at 10 PM, alone, with no one to think out loud with.

That's this week's issue.

THE OPENING SIGNAL

Getting stuck is part of running a business. Nobody talks about it much, but it happens constantly. You're circling a decision that won't resolve. A plan that isn't coming together. A problem you've turned over so many times you've stopped seeing it clearly.

Most of the time, you aren't missing information. You've simply spent so long inside the problem that every option starts sounding the same.

Most people handle this one of two ways. They push through alone, or they wait it out and hope clarity shows up eventually.

There's a third option, and it's more available than most business owners realize.

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WHAT ACTUALLY MATTERS

When I'm stuck, I don't open my AI tool looking for an answer. I open it because I need somewhere to think out loud. I still do this before strategy sessions, workshops, or anytime I'm trying to narrow several possible directions into one.

AI can act as a sounding board when you need to think out loud, and it doesn't replace trusted advisors. It's just available at 10 PM when you're spinning on a decision, which your advisors usually aren't.

That distinction matters more than it sounds. A sounding board isn't there to hand you a conclusion. It's there so you can hear your own thinking as you say it out loud, which is often the fastest way to notice where the real problem actually is.

Most business owners don't need more advice at 10 PM. They need a way to get the noise out of their head so they can finally see the real question they're trying to answer.

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ONE SMALL MOVE

Next time you feel stuck, try this prompt:

"I am stuck on [situation]. Help me identify what I am actually trying to solve and what might be getting in the way."

This works because it does the thing most of us skip when we're stuck: it separates the real problem from the noise around it. Half the time, what feels like being stuck is actually just an unclear problem wearing a bigger costume.

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WORTH PAYING ATTENTION TO

It turns out I'm not the only one using AI this way.

A recent industry survey covered by Digit.fyi found that a large share of executives now regularly turn to AI as a sounding board for business decisions, and most say it reduces their stress in the moment.

But the same research surfaced something worth sitting with: the more leaders leaned on AI for decisions, the more some of them started second-guessing their own instincts when AI's take differed from theirs.

That's the part I want you to notice. AI as a sounding board is genuinely useful. AI as a replacement for your own judgment is where it gets risky. The tool works best when you're using it to hear yourself more clearly, not when you're expecting it to make the decision for you.

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Try the prompt above the next time you're stuck on something this week, and reply to tell me what surprised you.

Here's the tension I keep noticing: most of us say we want a sounding board, but when we actually get one, we're tempted to treat its answer as the decision instead of the starting point. Which one are you more likely to do?

Talk soon,

Lucy

P.S. Being stuck isn't a productivity failure. It's just a normal part of thinking something through. Give yourself permission to use the tool without needing it to give you the whole answer.